Protecting Groups for Boronic Acids
INVENTORS • Ronald Raines, Brett VanVeller, Matthew Aronoff
WARF: P130142US02
View U.S. Patent No. 9,085,590 in PDF format.
Since its founding in 1925 as the patenting and
licensing organization for the University of Wisconsin-
The Wisconsin Alumni Research Foundation (WARF) is seeking commercial
partners interested in developing novel protecting groups for boronic acids
that make them easier to synthesize and use.
Madison, WARF has been working with business and
industry to transform university research into products
that benefit society. WARF intellectual property
managers and licensing staff members are leaders in
the field of university-based technology transfer. They
OVERVIEW
are familiar with the intricacies of patenting, have
worked with researchers in relevant disciplines,
understand industries and markets, and have
Boronic acids (i.e., compounds that have a single boron-carbon bond) are one of the most
useful functional groups in organic chemistry and chemical biology. They have
applications in polymer sciences, fine chemicals and pharmaceuticals.
negotiated innovative licensing strategies to meet the
individual needs of business clients.
Derivatives of boronic acids, called benzoxaboroles, are especially promising in medicine.
They may aid antifungal, antimalarial and other treatments. Some benzoxaboroles
currently are in preclinical and clinical trials.
Problematically, the unique characteristics that make boronic acids so valuable also make
them difficult to synthesize and utilize.
THE INVENTION
UW–Madison researchers have developed two novel protecting groups for boronic acids
that make them easier to synthesize, manipulate and use. Protecting groups prevent
undesired reactions.
Compound 1 is a divalent ligand to protect hemiboronic acids (e.g., benzoxaborole).
Compound 2 is a trivalent ligand that complements another popular trivalent protecting
group called MIDA (N-methyliminodiacetic acid). The protected boronic acids are liberated
by aqueous acid.
Boronic acids treated with either of the protecting groups become highly luminescent
when exposed to long-wave UV light, facilitating their use.
Wisconsin Alumni Research Foundation | 614 Walnut Street, 13th Floor | Madison, WI 53726 | [email protected] | www.warf.org
WARF: P130142US02
BUSINESS OPPORTUNITY
• Companies such as Sigma-Aldrich offer more than 100 distinct MIDA-protected boronates.
APPLICATIONS
• Synthesizing boronates
• Polymer sciences, fine chemicals and pharmaceuticals
KEY BENEFITS
• Makes boronic acids easier to synthesize and utilize
• The protecting groups are uniquely compatible with basic and reductive reaction conditions (potentially doubling usefulness in crosscoupling reactions).
ADDITIONAL INFORMATION
Related Technologies
WARF reference number P110315US02 describes a method using boronic acids to improve drug delivery.
WARF reference number P110055US02 describes a method using boronic acids for biomass conversion.
Tech Fields
Research Tools - Synthesis & purification
CONTACT INFORMATION
For current licensing status, please contact Jennifer Gottwald at [email protected] or (608) 262-5941.
Wisconsin Alumni Research Foundation | 614 Walnut Street, 13th Floor | Madison, WI 53726 | [email protected] | www.warf.org